Trimethyltin chloride → 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2-methyl-4-(trimethylstannyl)-1H-imidazole

HRID 1498327Notes

Reaction equation

[Si:1]([O:8][C:9]([CH3:19])([CH3:18])[CH2:10][N:11]1[CH:15]=[C:14](I)[N:13]=[C:12]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Br)C.[CH3:24][Sn:25](Cl)([CH3:27])[CH3:26]>C(Cl)Cl>[Si:1]([O:8][C:9]([CH3:19])([CH3:18])[CH2:10][N:11]1[CH:15]=[C:14]([Sn:25]([CH3:27])([CH3:26])[CH3:24])[N:13]=[C:12]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-iodo-2-methyl-1H-imidazole (1.5 g, 3.8 mmol) in DCM (15 mL) was added ethylmagnesium bromide (1.9 mL, 3 mol/L, 5.7 mmol) at −78° C. The temperature of the mixture was allowed to warm up to about 10° C. slowly and cooled again. Trimethyltin chloride (6.5 ml, 1 mol/L, 6.5 mmol) was added dropwise at −78° C. After the addition, the temperature was allowed to slowly warm up to room temperature. The reaction mixture was pouted into saturate NH4Cl solution, then extracted with DCM, The organic was washed with water twice, dried over anhydrous Na2SO4, concentrated to give 0.44 g of 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-2-methyl-4-(trimethylstannyl)-1H-imidazole. Yield=63%. 1H NMR (CDCl3, 400 MHz): δ 7.04 (s, 1 H, ArH), 3.74 (s, 2 H), 2.43 (s, 3 H), 1.24-1.20 (m, 6 H), 0.88 (s, 9 H), 0.29 (s, 6 H), 0.03 (s, 8 H). LC-MS: m/z=375 [M+H+]

Workup

temperaturecooled again
additionAfter the addition
temperatureto slowly warm up to room temperature
concentrationinto saturate NH4Cl solution
extractionextracted with DCM
washThe organic was washed with water twice
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-9f7485d02de64704bb7df3a8877c7c45
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09198918B2

Reaction notes

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